GB705670A - Dehydrating aqueous propynol by azeotropic distillation - Google Patents
Dehydrating aqueous propynol by azeotropic distillationInfo
- Publication number
- GB705670A GB705670A GB31395/50A GB3139550A GB705670A GB 705670 A GB705670 A GB 705670A GB 31395/50 A GB31395/50 A GB 31395/50A GB 3139550 A GB3139550 A GB 3139550A GB 705670 A GB705670 A GB 705670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propynol
- column
- benzene
- water
- distilled
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FWLKYEAOOIPJRL-UHFFFAOYSA-N prop-1-yn-1-ol Chemical compound CC#CO FWLKYEAOOIPJRL-UHFFFAOYSA-N 0.000 title abstract 8
- 238000010533 azeotropic distillation Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- FQOWXJIGHJQNSM-UHFFFAOYSA-N O.C(#CC)O Chemical compound O.C(#CC)O FQOWXJIGHJQNSM-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- KRQHFOPDMHSYCY-UHFFFAOYSA-N benzene prop-1-yn-1-ol Chemical compound C(#CC)O.C1=CC=CC=C1 KRQHFOPDMHSYCY-UHFFFAOYSA-N 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 2
- 238000006297 dehydration reaction Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- WXLISWSDZCCSQU-UHFFFAOYSA-N O.C1=CC=CC=C1.C(#CC)O Chemical compound O.C1=CC=CC=C1.C(#CC)O WXLISWSDZCCSQU-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
<PICT:0705670/III/1> In the dehydration of aqueous solutions of propynol by azeotropic distillation using benzene as entrainer, thermal decomposition of the propynol during distillation is prevented by adding a small proportion ( 1/4 to 1/2 per cent. by weight of the propynol) of succinic acid or hydrochloric acid to the distillant. The crude aqueous propynol obtained by reacting acetylene with formaldehyde in the presence of a catalyst and by distilling the product, may be treated with acidified methanol and the mixture then distilled in order to obtain a purified propynol-water azeotrope suitable for dehydration. Precautions are taken to ensure that vapours containing propynol do not come in contact with surfaces heated considerably above the boiling point. The propynol-water binary, containing a small proportion of H Cl, is introduced in fractionating column 1, which is charged with sufficient benzene to ensure that the upper part of the column is filled with the benzene-water-propynol ternary azeotrope. The ternary is distilled off at 69 DEG C., condensed in condenser 11, and the condensate is passed to a decanter where it separates into two layers. The benzene-propynol layer is returned to column 1, and the water-propynol layer is introduced into column 3. The propynol - water azeotrope is distilled from column 3 at 97 DEG C., and condensed in condenser 31. A portion of the condensate is returned as reflux to column 3 and the remainder is passed to column 1. The water obtained at the base of column 3 is rejected. The bottoms from column 1, which comprise benzene and propynol, are distilled in column 2. A benzene-propynol mixture at 78 DEG C. is removed from the head of column 2, and condensed in condenser 21. A portion of the condensate is returned as reflux to column 2, and the remainder is passed to column 1. Pure propynol is withdrawn from the base of column 2. Specifications 508,062 and 620,298 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US705670XA | 1949-12-30 | 1949-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB705670A true GB705670A (en) | 1954-03-17 |
Family
ID=22096081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31395/50A Expired GB705670A (en) | 1949-12-30 | 1950-12-27 | Dehydrating aqueous propynol by azeotropic distillation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB705670A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111807929A (en) * | 2020-07-20 | 2020-10-23 | 万华化学集团股份有限公司 | Separation method of 2-methyl-3-butyne-2-ol |
| CN113666803A (en) * | 2021-08-30 | 2021-11-19 | 四川众邦制药有限公司 | Method for synthesizing propiolic alcohol |
| WO2022016317A1 (en) * | 2020-07-20 | 2022-01-27 | 万华化学集团股份有限公司 | Separation method for 2-methyl-3-butyne-2-ol |
-
1950
- 1950-12-27 GB GB31395/50A patent/GB705670A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111807929A (en) * | 2020-07-20 | 2020-10-23 | 万华化学集团股份有限公司 | Separation method of 2-methyl-3-butyne-2-ol |
| WO2022016317A1 (en) * | 2020-07-20 | 2022-01-27 | 万华化学集团股份有限公司 | Separation method for 2-methyl-3-butyne-2-ol |
| CN111807929B (en) * | 2020-07-20 | 2022-08-05 | 万华化学集团股份有限公司 | Separation method of 2-methyl-3-butyne-2-ol |
| CN113666803A (en) * | 2021-08-30 | 2021-11-19 | 四川众邦制药有限公司 | Method for synthesizing propiolic alcohol |
| CN113666803B (en) * | 2021-08-30 | 2023-09-01 | 四川众邦新材料股份有限公司 | Method for synthesizing propargyl alcohol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB703065A (en) | Improvements in or relating to the dehydration of hydrazine by azeotropic distillation | |
| US3394058A (en) | Separation of formic acid and water from acetic acid by distillation with an entraine | |
| US2485329A (en) | Ether purification | |
| GB1000574A (en) | Process for the recovery of pure isophorone from reaction-mixtures by distillation | |
| GB705670A (en) | Dehydrating aqueous propynol by azeotropic distillation | |
| GB647927A (en) | Extractive distillation with salt solutions | |
| GB727078A (en) | Purifying acetic acid by azeotropic distillation | |
| US2477087A (en) | Separation and purification of methyl ethyl ketone | |
| GB719911A (en) | Purifying acrylonitrile by extractive distillation | |
| US1972579A (en) | Esters of 2-ethylbutanol-1 | |
| US3102905A (en) | Process for preparing tertiary butyl acetate | |
| GB937546A (en) | Recovery of dry methanol from solutions of dimethyl terephthalate | |
| US2808429A (en) | Synthesis of carbonyl compounds | |
| GB870012A (en) | Improvements in the purification of crude dimethyl terephthalate by distillation | |
| GB741216A (en) | Improvements in or relating to the concentration of aqueous hydrazine by distillation | |
| EP0001681A1 (en) | Dehydration of alcohols, preferably ethanol, using a cyclohexane entrainer | |
| US3036090A (en) | Catalyst and process for production of meta-dioxanes | |
| GB736984A (en) | Improvements in or relating to the dehydration of liquids by azeotropic distillation | |
| GB770551A (en) | Continuous esterification process | |
| US2527358A (en) | Process of purifying propargyl alcohol | |
| US2846025A (en) | Process for removal of divinylacetylene from acrylonitrile | |
| GB815091A (en) | Improvements in and relating to the separation of alcohols | |
| GB812963A (en) | Manufacture of low molecular carboxylic acid anhydrides | |
| GB762974A (en) | Dehydrating alcohols by extractive distillation | |
| GB671936A (en) | Propyl and isopropyl methacrylate |